Sodium Carbonate → Ethyl 7-(5-phenyl-3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate

To a solution of ethyl 7-(trifluoromethylsulfonyloxy)-3-azabicyclo[3.3.1] non-6-ene-3-carboxylate (0.12 g, 0.35 mmol) in dimethoxyethane (3 mL) was added saturated sodium carbonate solution (1 mL), lithium chloride (0.04 g, 0.9 mmol) and 5-phenyl-3-pyridinylboronic acid (0.12 g, 0.7 mmol). The flask was alternately evacuated and filled with argon three times. Then tetrakis(triphenylphosphine)palladium(0) (0.01 g, 0.01 mmol) was added, and the evacuation and argon fill was performed once again. The flask was then sealed under argon, and the stirred reaction mixture was heated at 95(C for 2 h. The mixture was cooled to ambient temperature, diluted with water (10 mL) and extracted with chloroform (3×5 mL). The combined extracts were dried over sodium sulfate and filtered. Concentration of the filtrate by rotary evaporation, followed by purification of the residue by silica gel column chromatography, using a gradient of chloroform/methanol (0-2% methanol) as eluent, gave ethyl 7-(5-phenyl-3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate as a light yellow oil (0.12 g, 90%).

1. customThe flask was alternately evacuated
2. additionfilled with argon three times
3. customThe flask was then sealed under argon
4. customthe stirred reaction mixture
5. temperaturewas heated at 95(C for 2 h
6. extractionextracted with chloroform (3×5 mL)
7. dry with materialThe combined extracts were dried over sodium sulfate
8. filtrationfiltered
9. customConcentration of the filtrate by rotary evaporation
10. customfollowed by purification of the residue by silica gel column chromatography

ORD 기록

ord-aa863c751a844839ae5e90cddf19ed49

출처 데이터셋

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07402592B2